Heart of Chicago Vacations from $417

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Your Heart of Chicago Vacation

Experience everything this neighborhood has to offer with a customized Heart of Chicago vacation package. However you see yourself spending your time here, you'll find countless opportunities for fun, adventure and relaxation. When it's time to explore the sights, you'll find a lot of awesome attractions nearby including University of Illinois Chicago, United Center and Anna and Frederick Douglass Park. Visit one, two or all during your trip to Heart of Chicago. No matter your travel plans or the size of your budget, booking your dream Heart of Chicago vacation is easy with Expedia.

The Latest Heart of Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
Save 100% on your flight
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
8.2/10 Very Good! (1,011 reviews)
Clean comfortable room. Pleasant staff. Nothing fancy or upscale but met our traveling needs for a clean & comfortable room. Breakfast choices limited good coffee.

Reviewed on Jul 23, 2025

The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (126 reviews)
We were attending a wedding at Geneva National, so it was very convenient. But particularly for the whopping $650 we paid, it was VERY underwhelming. Pretty old, and the smoke alarm went off when using a hair straightener! Ceiling fan was very rickety, noisy all night but needed because it was quite hot. Pictures are a bit deceiving, this is not a luxury property.

Reviewed on Jul 27, 2025

Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (CHI)
8.4/10 Very Good! (999 reviews)
Very disappointed with the lack of dining options and the fact that there’s no complimentary coffee or water available in the lobby. We will not stay here again

Reviewed on Jun 10, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The hotel was nice, staff were friendly and the overall stay was excellent and convenient to walk.

Reviewed on Jul 28, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Very nice location super friendly staff very modern and clear hotel

Reviewed on Jul 27, 2025

Where to stay in Heart of Chicago

Find the best Heart of Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Heart of Chicago
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Heart of Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $199 total per night from Aug 10 to Aug 11
$199 total
Aug 10 - Aug 11
Total includes taxes and fees
7.8/10 Good! (9,030 reviews)
"There are areas of the property outside that need some tlc. The hallways are outdated in decor but the room was clean and comfortable. The reception area was very pretty. The staff was courteous and friendly. The hotel itself has a good location walkable to the Soldier Field which we were in town ..."

Reviewed on Jul 29, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
$261 nightly
The price is $301 total per night from Aug 17 to Aug 18
$301 total
Aug 17 - Aug 18
Total includes taxes and fees
9/10 Wonderful! (2,137 reviews)
"Elevator"

Reviewed on Jul 28, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $169 total per night from Aug 10 to Aug 11
$169 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (2,566 reviews)
"I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, ..."

Reviewed on Jul 29, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,660 properties in Heart of Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Heart of Chicago

Canalport Riverwalk Park

After visiting Canalport Riverwalk Park, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.

Canalport Riverwalk Park

Mexican Fine Arts Center Museum

You can spend an afternoon studying the exhibits at Mexican Fine Arts Center Museum in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Mexican Fine Arts Center Museum

Things to do

Artisan Italian Pasta Class in Chicago

Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)

$119
per adult
Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)
River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.